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Greatest Hits Oldies But Goodies Ever

In 1958, Roy Orbison used what little money he had to buy out his contract at Sun Records, trading a label deal for the back seats of parked cars. After his 1956 single “Ooby Dooby” charted, Sun owner Sam Phillips pushed the shy, nearsighted singer in thick glasses to shout and gyrate like Elvis Presley or Jerry Lee Lewis. Refusing to spend his career faking wild rockabilly on stage, Orbison paid his way out of the contract and walked away broke. His young wife, Claudette, was expecting their first child, and relatives urged him to quit music for a steady paycheck in the West Texas oil fields where his father worked. Orbison had studied geology at North Texas State College with that very path in mind, yet he chose to keep driving overnight between Texas and Nashville’s Music Row to pitch songs for Acuff-Rose and send small checks home. With no money for motels, he slept in the back of friends’ cars or on the apartment floor of his songwriting partner, Joe Melson, before smoothing out his suit each morning to audition ballads that executives called too slow for radio. A brief deal at RCA Victor brought more commercial failures, until producer Chet Atkins realized RCA did not know how to use Orbison’s operatic voice and steered him toward Fred Foster at the new independent label Monument Records in 1959. Back home in Odessa, Texas, Orbison and Melson sat for hours inside a car parked at the curb, building orchestral ballads around his natural range. After Elvis Presley and the Everly Brothers both turned down their new song, “Only the Lonely,” Foster let Orbison record it his own way with strings in the spring of 1960. The record reached No. 2 in the United States and No. 1 in Britain, proving that the quiet Texan standing still behind the microphone never needed to imitate anyone else.

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When Sun Records engineer Jack Clement listened to Roy Orbison sing a slow ballad named “The Clown” in Memphis, he told the young Texan outright that he would never make it as a ballad singer.

At the time, Sun owner Sam Phillips was building an empire on the wild rockabilly of Elvis Presley, Jerry Lee Lewis, and Carl Perkins. Orbison had scored a No. 59 single on the label in May 1956 with “Ooby Dooby,” which sold roughly 200,000 copies, yet he was a shy, nearsighted guitarist in thick corrective glasses who hated jumping around on stage.

After his subsequent Sun singles failed to chart and his band, the Teen Kings, broke up in late 1956, Orbison grew tired of forcing a loud rockabilly delivery that did not fit his natural voice. In 1958, he used his own money to buy back his recording contract from Phillips and walked out of Memphis on his own.

That decision left the twenty-two-year-old singer nearly broke just as his teenage wife, Claudette Frady, was expecting their first son, Roy Dewayne, who arrived on September 16, 1958. Back in West Texas, relatives urged him to give up music and take a dependable oil field job like his father, Orbie Lee, especially since Roy had studied geology at North Texas State College for that exact fallback.

Instead, Orbison signed as a staff writer with publisher Wesley Rose at Acuff-Rose Music in Nashville. Early in 1958, he pitched a love song written for his wife titled “Claudette” to the Everly Brothers, who placed it as the B-side to their smash hit “All I Have to Do Is Dream”.

Although that songwriting royalty check briefly lifted his spirits, the money ran out quickly, forcing Orbison and his young family to move in with his parents in Wink, Texas, before renting a tiny apartment in Odessa. One day in 1958, local musician Joe Melson tapped on the window of Orbison’s car in Odessa and suggested they try writing together.

Because Orbison’s cramped apartment left no quiet space to work with a newborn inside, the two men turned the front seat of his parked car into their daily studio. Whenever they drove the long overnight stretch to Nashville to pitch their material, they lacked the cash for motel rooms, sleeping in the back seats of cars or on floors before smoothing out their suits for morning appointments on Music Row.

Even experienced Nashville hitmakers were puzzled by his quiet demeanor. Songwriter Boudleaux Bryant recalled Orbison singing softly and bashfully at auditions, as if he were afraid someone in the office might be disturbed and reprimand him.

Wesley Rose still believed in him and arranged a three-session deal with Chet Atkins at RCA Victor in 1958. Across seven recordings, RCA released only two singles, “Seems to Me” and “Almost Eighteen,” both of which missed the charts entirely.

Realizing RCA had no idea how to frame Orbison’s multi-octave voice, Atkins and Rose steered him in mid-1959 toward Fred Foster, who had just launched an independent label called Monument Records. At their first session in June 1959, they cut “Paper Boy,” followed in September by the Orbison-Melson collaboration “Up Town,” where Foster brought in strings and the Anita Kerr Singers to surround Roy’s voice.

“Up Town” reached No. 72 on the pop chart in early 1960, giving Orbison his first national chart appearance in more than three years and convincing Foster to take a bigger gamble. Back in Texas, Orbison and Melson wrote a sweeping dramatic ballad called “Only the Lonely (Know the Way I Feel)”.

Hoping for a major payday, they drove to Memphis to pitch the song to Elvis Presley, only to wait outside Graceland while Presley slept through the appointment. They next offered the ballad to the Everly Brothers in Nashville, who turned it down because they wanted to record one of their own compositions instead.

On March 25, 1960, inside RCA Studio B in Nashville, Foster placed Orbison in front of top session players including pianist Floyd Cramer, guitarists Hank Garland and Harold Bradley, bassist Bob Moore, and drummer Buddy Harman. Rather than asking Orbison to shout like a rockabilly frontman, Foster let him build from a gentle verse to a soaring operatic falsetto.

Released in May 1960, “Only the Lonely” climbed to No. 2 on the Billboard Hot 100 and hit No. 1 in the United Kingdom that October, launching a run of Monument classics that included “Running Scared,” “Crying,” “In Dreams,” and “Oh, Pretty Woman”. By betting on his own voice during those lean years between parked cars in Odessa and studio doors in Nashville, Roy Orbison proved that standing dead still behind a microphone was more than enough.

http://www.youtube.com/watch?v=D3a8Seh3Cp4

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On February 22, 1968, Johnny Cash stopped his band in the middle of a song in London, Ontario, refusing to play on until June Carter agreed to marry him. Cash had been asking since they first met backstage at the Grand Ole Opry in 1956. Over the next twelve years, he proposed at least 30 times, and Carter always said no. When his addiction to pills and alcohol nearly killed him, Carter and her parents moved into his home, took away his drugs, and stayed up through the nights to watch over him, though she refused to become his wife until he got clean. By early 1968, Cash had turned his life around, recording his live album at Folsom Prison in January with Carter singing beside him. A month later in Canada, he carried a diamond ring in his suit pocket for days, waiting for a moment where she could not dodge the question or slip backstage. At the London Gardens arena, in front of 7,000 fans, he stopped their Grammy-winning duet “Jackson” and pulled out the ring. Carter had grown up performing with her family and knew how to handle any crowd, yet she blushed, clasped her hands together, and tugged at his coat sleeve, urging him to keep singing. Cash waited at the microphone while 7,000 people cheered for an answer. After she finally said yes, the two held hands backstage and decided to fly to the Bahamas the very next day. One week later, on March 1, 1968, they married at a church in Franklin, Kentucky. They stayed together on the road and at home for 35 years, until Carter passed away in May 2003 and Cash died four months later.

In 2003, Toby Keith stepped onto Willie Nelson’s tour bus in Las Vegas to celebrate their number one duet and ended up missing his flight the next morning. That week, “Beer for My Horses” was in the middle of a six-week run atop the Billboard Hot Country Songs chart. The two had gathered in Vegas for the Academy of Country Music Awards and a television special marking Nelson’s 70th birthday. After the show, Nelson invited his younger singing partner aboard his famed bus, Honeysuckle Rose. Standing over six feet tall, Keith carried the reputation of a burly Oklahoma powerhouse who could hold his own anywhere. He had actually quit smoking years earlier to keep up with his work schedule, yet nobody in country music said no when Willie Nelson offered to share on his own bus. It took very little to knock the younger star flat. Dizzy and overwhelmed, Keith made his way back to his room at the Mirage, slept for hours, and missed his plane the following day. Once he woke up aboard his own bus, Big Dog Daddy, he told the whole story to his longtime guitarist and co-writer Scotty Emerick. Laughing at the misadventure, the pair grabbed acoustic guitars and wrote “I’ll Never Smoke Weed with Willie Again.” Before releasing it, Keith played the demo for Nelson to make sure the joke landed right. Nelson laughed until tears came to his eyes and gave his full blessing. Keith included the recording as a hidden bonus track on his November 2003 album Shock’n Y’all, and fans requested it at his shows for the next twenty years. Even after Keith passed away in February 2024, that night in Vegas stayed with listeners as a favorite memory of a superstar who never minded making himself the punchline alongside his hero.

A week after September 11, Toby Keith wrote Courtesy of the Red, White and Blue in twenty minutes on the back of a fantasy football sheet. Six months earlier, in March 2001, his father, Hubert K. Covel Jr., died in a highway crash involving a bus with failed brakes. An Army veteran who lost an eye in service without ever complaining, Covel raised the American flag in his Oklahoma yard every morning. When the September 11 attacks occurred, Keith was still mourning that sudden loss and wondering how his father would have responded. At home with his guitar, Keith placed his father at the center of “Courtesy of the Red, White and Blue (The Angry American).” Initially, he refused to record it commercially, worried listeners would think he was profiting from his father’s death and national tragedy. He kept the song private, playing it acoustically only for young troops preparing to deploy. Late in 2001, Keith performed the song at the Pentagon and Marine Corps headquarters, where troops stood cheering in tears. Afterward, Marine Corps Commandant General James L. Jones put a hand on Keith’s shoulder and told him it was his civic duty to release the song for the nation. Keith released it in May 2002 as the lead single from his album Unleashed. The song hit No. 1 on the Billboard Hot Country Songs chart and entered the Billboard Hot 100 Top 25. Those early military performances also led Keith toward eleven USO tours to frontline bases in Afghanistan and Iraq. Written on scrap paper as a goodbye to one Oklahoma veteran, the song carried the memory of his father raising the morning flag to thousands of troops overseas.

Halfway through a 2014 concert on his Shut Up and Hold On Tour, Toby Keith stopped the music and invited a wounded combat veteran onto the main stage. Working with The Independence Fund, Keith surprised the soldier, who had lost both legs in service, with a $15,000 Action Trackchair in front of thousands of fans. Built with heavy treads instead of standard wheels, the chair was engineered to cross mud, sand, snow, and wooded trails where ordinary hospital wheelchairs could never roll. After handing over the keys, Keith leaned down to hug the veteran at eye level and stepped back from the microphone, asking the arena to stand and salute the man in the center of the stage. That night was not a single publicity stop. Through an ongoing partnership with The Independence Fund, Keith helped present tracked chairs to severely wounded veterans at multiple concerts across the country. That dedication came directly from the way he was raised. His father, Hubert K. Covel Jr., was a United States Army veteran who lost an eye during military service and died in a car accident in March 2001. Honoring his father’s memory, Keith spent years separating politics from the people in uniform, flying into remote bases on eleven USO tours to play for more than 250,000 troops in Iraq and Afghanistan. For the men and women who rolled off his stage in an Action Trackchair, the moment lasted far beyond a night of country music. Once they returned home, those treads meant a husband or father could head back into the woods, reach the edge of a fishing lake, or take his kids across a park without waiting for someone else to push.

In 1999, Nashville executives told Toby Keith that his new music had no commercial future, so he used his own money to buy back the album and walk away. At the end of the 1990s, Mercury Records wanted polished pop country built for easy radio play. Keith, a former Oklahoma oil field hand, had gone into the studio with something much louder. Working with songwriter Chuck Cannon, he had written a defiant track titled “How Do You Like Me Now?!” and built an entire album around that unapologetic sound. When he played the finished tapes for the label brass, the executives turned the project down flat, arguing the lead song was too brash to sell. Rather than letting the music sit on a shelf or softening his style to protect a major contract, Keith bet on himself. He used his own savings to purchase the master recordings from Mercury and walked out a free agent. Carrying an album that his old label had just written off, he met with producer James Stroud at the newly launched DreamWorks Records Nashville. Stroud believed in the recordings immediately and signed Keith, agreeing to release the project without changing a single note. Sent to radio in late 1999, “How Do You Like Me Now?!” caught fire with listeners from small town bars to highway pickup trucks. The single climbed to No. 1 on the Billboard Hot Country Songs chart, held the top spot for five straight weeks, and finished 2000 as the biggest country song of the entire year. A track written about proving doubters wrong ended up doing the exact same thing for the man singing it. By putting his own money on the line for those master tapes, Keith launched the defining decade of his career on his own terms.

At a remote desert outpost with no stage or sound system, young soldiers planted spent mortar shells in the sand to build Toby Keith a place to sing. Across eleven USO tours in Iraq and Afghanistan, Keith performed for more than 250,000 American service members. While many entertainers stayed at larger rear bases with full production crews, he repeatedly boarded military helicopters to reach small forward operating bases near the front lines. Many of those outposts had nothing ready for a visiting musician. At one desert camp, troops gathered empty mortar casings still darkened by powder and set them upright in the dirt. Inside the scorched metal tubes, they wedged flashlights aimed toward the night sky, turning a patch of dry ground into a makeshift amphitheater. Keith stepped into that circle of light with just an acoustic guitar. No security barriers stood between the performer and the unit. Sitting on an ammunition crate as red desert dust coated his boots and the neck of his guitar, he sang for troops who were mostly in their early twenties. As the evening went on, the yellow beams from the shell casings lit up dusty uniforms and quiet, homesick faces gathered shoulder to shoulder. Keith stayed right there with them, sharing water and trading stories about home in the calm between patrols. Packed arenas and radio hits built his career in the States. Still, year after year, Keith returned to the places where an acoustic guitar and a row of flashlights in empty shells meant a piece of home had found its way to the front lines.

When a July 2022 cycling accident left Amy Grant unable to recall songs she had sung for forty years, Vince Gill cleared his schedule to help her start over. The fall happened on July 27 at Nashville’s Percy Warner Park after her bicycle wheel hit a pothole, leaving her unconscious for ten minutes despite her helmet. She spent two nights at Vanderbilt University Medical Center with a traumatic brain injury, just two years after undergoing open-heart surgery in June 2020 for a congenital defect. Back home, the lingering effects of the concussion took hold. Sensitivity to light and noise kept her in a quiet room with the curtains drawn, while balance issues forced an avid walker to move one slow step at a time. Worse still, short-term memory loss erased family stories, the names of longtime colleagues, and the words to songs from her four-decade career. Vince immediately postponed her fall tour and canceled his own upcoming performances, turning off electronics and limiting visitors at their Nashville house. Every afternoon, he walked beside her with an arm around her waist to steady her down the hallway and along the garden path. When she cried in the dark and asked if this was all she had left, he held her and promised to do the remembering for her while she began writing daily notes in a journal. By November and December 2022, she was ready to attend the Kennedy Center Honors and join him for their annual Christmas at the Ryman residency. Vince placed large notebooks and a teleprompter in front of her onstage, staying close enough to rest a hand on her shoulder and cover any brief pause with gentle humor until she found her next line.

In 1975, while country radio was filled with songs about barroom infidelity and broken marriages, Don Reid wrote a ballad about keeping a wedding vow until the end of life. Released as a single from The Statler Brothers’ album The Holy Bible: Old Testament, “I’ll Go to My Grave Loving You” climbed to number three on the Billboard Hot Country Singles chart and became one of the quartet’s biggest records of the 1970s. Don drew the song from his own marriage to his high school sweetheart, Brenda, back home in Staunton, Virginia. With his older brother Harold anchoring the bass and Phil Balsley and Lew DeWitt completing the four-part harmony, the record sounded less like a stage performance and more like a quiet promise made in a living room. Eighteen years later, the brothers returned to that same theme from the other side of middle age. By 1993, as the group members entered their fifties and sixties, Don and Harold Reid sat down together to write “I’ve Never Lived This Long Before” for their album Home. Backed by Phil Balsley and tenor Jimmy Fortune over a sparse, unhurried arrangement, the two men traded their usual stage humor for an honest look at graying hair and the quiet surprise of growing old. Where the 1975 hit carried the steady voice of a young husband looking ahead, the 1993 recording sounded like two longtime partners talking across the dinner table after decades together. Rather than chasing a younger crowd in the 1990s, The Statler Brothers chose to age right alongside the people who bought their records. Those two songs, recorded eighteen years apart, went on to be played at countless silver and golden wedding anniversaries and funeral services across America, giving couples the words for both the promise of youth and the gratitude of old age.

Long before Conway Twitty earned 40 number one singles on the Billboard country charts, an elderly Black neighbor in the Mississippi Delta taught a six-year-old white boy how to play the blues on a cheap Sears & Roebuck toy guitar. Born Harold Lloyd Jenkins on September 1, 1933, he grew up during the Great Depression in Friars Point, Mississippi. His parents, Mississippi River ferryboat captain Floyd Jenkins and his wife Velma, raised their family among one of the few white households in a community of Black cotton pickers and sharecroppers. When Harold’s grandfather, Papaw McGinnis, ordered him a mail-order guitar with stiff steel strings around age four or five, the boy took it next door to an older neighbor he respectfully called Uncle Fred. After long days working in the cotton fields, Uncle Fred sat on his wooden porch with an old guitar and a harmonica, showing the boy how to press the strings without hurting his fingers and how to slide a glass bottleneck or pocketknife blade along the neck. Even under the strict racial segregation of the Jim Crow South in the late 1930s, Floyd and Velma Jenkins encouraged their son to learn from Uncle Fred and treat him like family. On Sunday nights, the Jenkins family stood outside the open windows of the local Black church to listen to the gospel choir, while young Harold also absorbed the rhythms drifting from nearby juke joints. When the family moved across the river to Helena, Arkansas, in 1943, the ten-year-old carried those Delta blues and gospel lessons into his first band, the Phillips County Ramblers. Decades later, whenever interviewers asked where he found the low vocal growl and phrasing that carried him from 1950s rockabilly to the top of country radio, Twitty pointed back to Uncle Fred on that wooden porch in Friars Point.